The goal of this project is to study the solution reactions of diol epoxides derived from polycyclic aromatic hydrocarbons, in addition to model epoxides possessing well-defined structural properties. Among those reactions studied will be acid-catalyzed and spontaneous hydrolyses, and addition of nucleophilic reagents. Kinetic solvent and Alpha-deuterium isotope effects will be utilized to provide information about the rate-limiting steps, and the effectiveness of general acids in catalyzing the hydrolysis of polycyclic hydrocarbon expoxides, as a function of the structure of the general acid, will be studied. The information gained from the study of polycyclic hydrocarbon epoxide and model expoxide reactions under carefully defined conditions will greatly aid in our understanding of the reactions of carcinogenic epoxide metabolites under biological conditions, and with biological macromolecules.